0 Bedrooms for 1 Guest
Price $10 - $1000+

3,097 Siesta Key Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Siesta Key holiday rentals from 12 rental sites including HomeAway, TripAdvisor, Booking.com, and more, ranging from $28 to $2142 a night. 
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    Information about Siesta Key

    About Siesta Key

    Siesta Key is a small barrier island off the coast of Florida with the Gulf of Mexico on the west and Roberts Bay to the east. Only about 3.5 square miles, Siesta Key has a relaxed, suburban atmosphere that draws tourists and locals who want to get away from it all, but still have easy access to mainland amenities.

    Things to do in Siesta Key

    Siesta Key is best known for its warm, clear beaches. Siesta Key Public Beach, voted the 3rd Best Beach in the US by TripAdvisor users, is the most popular on the island. While this long-time favorite and nearby Crescent Beach are known for their soft, spotless sand, Turtle Beach is hailed as the perfect place for collecting shells. Surfing, volleyball, scuba diving, fishing, boating, jet skiing, and even parasailing are all beach activities available at one or more beaches on Siesta Key. Downtown hosts a wealth of dining and shopping options from family-friendly restaurants to a host of clubs and nightlife spots. Explore the island’s natural beauty with a hike, bike ride, or walk to the Point of Rocks to spot rare marine life and birds.

    Siesta Key Accommodations

    Even though it is an island, Siesta Key is not difficult to reach. Fly into the Sarasota-Bradenton International Airport, just 8 miles from the center of Siesta Key, and drive into town via one of the two drawbridges that connect it to the mainland. If you want to get started on your vacation right away, you can even take a ferry or boat from nearby Sarasota. Finding a vacation rental with a view or pool within your price range will not be a challenge with Tripping’s wide variety of properties available on Siesta Key!

    Vacation Rentals in Siesta Key

    Looking for the perfect vacation rental for your Siesta Key getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Siesta Key offers 3,095 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 2,244 properties with high-speed internet, 1,679 full with jacuzzi and pool, and NaN homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

    For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $4637 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Siesta Key has 3,095 gorgeous homes with 481 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

    Search properties from 12 rental sites in Siesta Key where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 1,564 HomeAway rentals, 712 TripAdvisor short term rentals and 457 Booking.com vacation rentals.